Water insoluble azo dyestuffs derived from dihydrobenzocarbazoles



Patented Sept. 22, 1936 um-Tao STATES PATENT OFFICE WATER INSOLUBLE AZO DYESTUFFS DE- RIVED FROM DIHYDROBENZOCARBA- ZOLES Wilhelm Neelmeier, Leverkusen-Wiesdorf, Hein-' rich Morschel, Cologne-Deutz, and Otto Goll, Leverkusen-I. G.-Werk, Germany, assignors to a General Aniline Works, Inc., New York, N. Y.,

a corporation of Delaware Application February 13,1933,

No Drawing.

Serial No. 656,625. In Germany February 18,

The present invention relates to new waterinsoluble azodyestufis, more particularly it relates to dyestuffs which may be represented by the probable general formula:

wherein R, stands for a non-.sulfonated and noncarboxylated aromatie radical, such as' a radical of theibe nzenau naphthalene or carbazole series, and R" stands for the radical of a nonable by coupling in substance or on a substratum a diazoti zed non sulfonated and non-carboxylatedzaminer suitable for producing azodyestuffs with a Z-hydrdxy-5,6 dihydro-Z8-benzocarbazole-3-carboxylic acid "arylamide. The shades, when produced on the fibre, are distinguished by good fastness properties.

The coupling components used in our invention have been described and claimed in the application for Letters Patent Serial No. 656,623, filed February 13, 1933, and entitled: New dihydrobenzocarbazole compounds, two of us being joint inventors in said application. They are obtainable by carbonating 2-hydroxy-5,6-dihydro-7,8-benzocarbazole by a treatment with carbon dioxide in the presence of an alkali metal carbonate at superatmospheric pressure and an elevated temperature and condensing the 2- hydroxy- 5, 6 dihydro -7,8-benzocarbazole-3-carboxylic acid formed with non-sulfonated and non-carboxylated primary aromatic or heterocyclic amines by dissolving the said carboxylic acid and said amine in an inert organic solvent, adding an acidor water-binding agent and heating to an elevated temperature in order to form the corresponding arylamides.

8 Claims. (01. zoo-46.1)

The invention is illustrated by the following example, without being limited thereto:

---Example.20 grams of well boiled and dried cotton yarn are impregnated for half an; hour in onelitre of a bath containing, 2,5 grams of 1- 3'-carbonylamino)-4-methoxybenzene, ccs. of

aqueous caustic soda of 34 B. and 10 cos. of

Turkey red oilof 50% strength; well squeezed and, without drying, introduced for about half an hour into a diazo solution of 1 litre, prepared t in the usual manner by diazotizing 2.5 grams of 2,5 -dichloro-l-aminobenzene, and neutralizing the mineral acid by the addition of sodium acetate. The cotton is then rinsed, soaped in a boiling bath and dried. A beautiful orange brown of good 'fastness properties is thus obtained.

The dyestufi probably has the following for- In the followingtable there; are given some further combinations and their shades, obtainable in an analogous manner:

Coupling component 53332 1 532 Shade 1 (2' hydroxy 5',6 dihydro- 4 chloro 2 Reddish 7,8 benzocarbazole 3' car amino l yellowish bonylamino) 4 mothoxyben methylbenzene. brown. zeno.

Do 6 chloro 2 Yellowish amino l brown. methylbenzene.

Do 4 chloro 2 Brown.

amino 1 methoxybenzenev Do 3,2-dimethyl-4- Reddish aminoazobenbrown. zene.

Do 2-1aminonaphtha- Brown.

one.

1 (2' hydroxy 5,6 dihydro 2,4 -dimethyl-2- Dark red- 7',8 benzocarbazole 3' car nitro -3 meth d i s h bonylamino) 2 methylbem oxy 4 amino brown. zone. azobenzene.

Coupling component ggggggg? Shade 1 (2 hydroxy 5,6' dihydro 4 nitro -2-amino- Yollowish 7,8 benzocarbazole 3 car 1 methylben brown. bonylamino) 2 methylben zene. zene.

1 (2' hydroxy 5,6 dihydro 6 chloro 2 Reddish 7',8 benzocarbazol 8' -,car amino l yellowish bonylamlno) 4 chlorobenzene. methylbenzene. brown.

Do (S-amino-i-ben- Orange zoylamino 1,3 brown. dimethylben- 1 (2' hydroxy 5',6' dihydro 3-chlo'roaniline Yellowish 7,8 benzocarbazole 3 car Y brown. bonylamino) chlorobenzeue.

Do 4 ehloro 2 Do.

amino 1 methylbenzene.

1 (2 hydroxy 5,6 dihydro 4-nitro 2 amino- R e (1 dis I1 7,8 benzocarbazole 3 car 1 methylben yellowish bonylamino) 2 methyl 4 zene. brown. methoxybenzene. 7

Do 6 chloro 2 Yellowish amino l brown. methylbenzene.

1 (2 hydroxy 5,6 dihydro 4 chloro 2 -tolu- Do.

7,8 benzocarbazolo 3 car idinebonylamino) 3 nitrobenzene.

2 -(2' hydroxy 5'45 dihydro 2-chloroanilinei Do.

7,8' beuzocarbazole 3' car bonylamino)naphthalene.

i (2" hydroxy 5,6 dihydro- 4 nitro 2 anisi- Brown.

7,8' benzocarbazole 3 car dine. bonylamino-)-carbazole.

We claim: 1. -Water-insoluble dyestufis of the general formula:' I

' claim 2.

' wherein R and R" stand for non-sulfonated and non-carboxylated radicals of the benzene or naphthalene series, yielding, when produced on the fibre, various shades of good fastness properties. 25

4. The dyestufi of the formula: j

HI 30 H26 oo-NH 0 om N/ on or I V i N=N yielding, when produced on the fibre, orangebrown shades ofgood fastness properties. 5. Fibre dyed with a dyestuff as claimed in claim 1. V 6. Fibre dyed with a dyestufi as claimed in 7. Fibre dyed with a claim 3.

8. Fibre dyed claim 4.

dyestufi as claimed with the dyestufi as claimed in WILHELM NEELMEIER; m

HEINRICH MORSCHEL. OTTO GQLL. 

